Voyage Filters

Make a scene at Dartmouth Regatta – Set the red sails of a Brixham trawler

Berth price

Single Berth Per Person



Embark Disembark Vessel DurationVoyage No
Thu 24-08-2023, 12:00Brixham, UK Sun 27-08-2023, 12:00Brixham, UK Pilgrim 3 NightsPM240823

Be centre stage as you watch the festivities of the Royal Dartmouth Regatta and enjoy some relaxing sailing. The 100ft original Brixham Trawler is a powerful vessel under sail as she was designed to trawl under sail. She will be centre stage purely due to her size and distinctive profile amongst the yacht fleets racing. You can enjoy sailing in and out and stealing the limelight. Dartmouth is one of those West Country historic ports that is perfect for showcasing boats out on the water. This deep estuary was once a steep sided valley until the sea level rose and created one of the most popular sailing harbours in the UK.

  • Voyage
  • Vessel

Ideal Voyage for ..

This is the ideal voyage for fun like minded sailors with or without experience. Pilgrim will provide you with the best seats in the house at the Royal Dartmouth Regatta where you can view the competitive sailing, rowing, water polo and firework display.

Lots of sailing and delicious food provided on board by Pilgrims resident chef! 


  • 74ft length on deck historic sailing trawler
  • Friendly and helpful instruction
  • Freshly cooked food and accommodation all onboard.
  • Comfortable berths
  • Free seats at the Dartmouth Regatta
  • Relaxed sailing
  • Great food


Vessel type / Rig Gaff Ketch
Guest Berths 10
Beam 17.5ft
Draft 10.5ft
Deck Length 74ft
Overall Length 94ft
Tonnage 90 tons
Year Built 1895
More about the Vessel

Voyage Description


This is the ideal voyage for fun like minded sailors with or without experience. Pilgrim will provide you with the best seats in the house at the Dartmouth Regatta where you can view the competitive sailing, rowing, water polo and firework display. Lots of sailing and delicious food provided on board by Pilgrims resident chef! 


  • 74ft length on deck historic sailing trawler
  • Friendly and helpful instruction
  • Freshly cooked food and accommodation all onboard.
  • Comfortable berths
  • Free seats at the Dartmouth Regatta


The Port of Dartmouth Royal Regatta always lives up to its reputation with superb on the water events and brilliant entertainment.

The focus of the Regatta has always been the sailing, rowing and swimming . This was the basis on which the first ever event was held in 1822! Since then a wide range of additional water and land based events have been added, making it a real highlight on the annual Regatta circuit.

This special short break covers the whole of the spectacular Dartmouth Regatta to include the famous regatta firework displays that are a real sight to behold – especially from the deck of a member of the National Historic Fleet!

During the sailing part of your days, we are very happy for you to get as involved in sailing Pilgrim as you would like to. There are plenty of opportunities to help the crew hoist the sails and even take the helm – or you may prefer to just sit back, relax and enjoy the view – it’s up to you!

Whatever you decide, enjoy the magnificent scenery as we leave Brixham, Torbay and set sail around Berry Head. This whole area is designated as an area of outstanding natural beauty. It is home to a sea bird colonies of guillemots, black legged kittiwakes, kestrels and gulls.  On our way to Dartmouth, we are often accompanied by dolphins or porpoises, so make sure you are up on deck with your camera to get some great shots of the amazing sea life.

Sailing past Berry Head, look for the lighthouse built in 1906 which has the distinction of being the smallest, highest and deepest lighthouse in the British Isles.  It is over 16 feet high and its white light can be seen for 14 nautical miles. Berry Head is also the site of a Napoleonic Fort built between 1794 and 1804.  Designed to protect Torbay from the French in the days when Torbay was a strategic naval anchorage.

Enjoy the seascape and dramatic coastal scenery with interesting rock formations creating rugged limestone cliffs, sandy bays, coasta­­­l coves and inlets.  We sail past St Marys Bay, a popular caravan holiday destination, the dramatic headland of Sharkham Point and then, hidden from view, the National Trust property of Coleton Fishacre, once the home of the Doyle Cart family.

A ‘Day Mark’ built in 1864 on the eastern side of the estuary helps us identity the River Dart.  We then pass the Mewstone rock just outside the mouth of the river.  This is often another spot to see the occasional harbour porpoise, common grey seal as well as cormorants, guillemots, gannets and sea gulls.

The rocky entrance to the r­­­­­­­iver is guarded on the west side of the estuary by a 15th Century castle, which also incorporates the church of St Petrox.

Kingswear, the harbour town directly opposite Dartmouth has its own historic castle. During the 2nd world war, the two fortifications were linked by chains at dusk to damage enemy ships attempting to attack Dartmouth.

Further up river The famous Britannia Royal Naval College sits above Dartmouth where officer training has taken place since 1863.

Other picturesque sailing areas that are within reach of Dartmouth include Slapton Bay and Salcombe Harbour or we can also sail up river to Dittisham and Conyton Fishacre the famous riverside residence of Agatha Christie.

Dartmouth Firework display on Pilgrim
Dartmouth Firework display on Pilgrim

During the weekend you will experience everything from illuminated vintage vessel parades to gig racing, many classes of yacht and dingy races, aircraft displays and fly pasts and of course the famous firework displays on the Thursday and Saturday evenings.

As you depart Dartmouth and set sail once more for Brixham you can relax with some peaceful sailing before stepping ashore.

Pilgrim crew learning the ropes.
Pilgrim crew learning the ropes.



On a sailing voyage we never use the word itinerary, as skippers will always be aiming for the best sailing and shore landings for the forecast and most idyllic or sheltered anchors and ports. They are as keen as you to include some of the highlights described below, but you have to go with Mother Nature, not fight her. The description above is based on what we think might be possible, based on past trips, or experience, but nothing is guaranteed on a sailing voyage.


Whether you are an experienced sailor or a complete beginner, the professional crew will train you to be guest crew from the moment you arrive, with the intention that everybody works together to sail the ship. The common thread to all Classic Sailing holidays is ‘Hands on’ participation on ships that use ropes, blocks and tackles and ‘people power’ to set sail.


We cater for a wide range of ages and physical abilities and how much you are expected to do varies a bit between vessels. See the vessel tab above which explains all about the ‘sailing style’ and what to expect in terms of hands on participation. There is a lot of information about day to day life, the ships facilities and accommodation on the vessel pages.


Every customer sailing with us will need to fill in basic medical questions on their booking application. If you are not sure if your current level of fitness and agility are up to a voyage, then please ring the Classic Sailing Office on 01872 58 00 22 and we can chat through your concerns and possibly find options that might suit you better.


  • Skipper & professional crew
  • Personal Safety Equipment
  • Sailing Instruction
  • All meals, snacks and refreshments
  • Port and landing fees
  • Linen and duvets
  • Third Party liability insurance


  • Travel to Joining Port
  • Travel from end port
  • Alcoholic Drinks
  • Towels
  • Waterproofs
  • Personal Travel Insurance



Start & End Port

Brixham, UK

Joining or leaving point.

Assemble towards the end of the Events Pontoon Red Point above. Zoom in to your ship!

For Pilgrim, your boat will be berthed on Brixham Town Pontoon, on the east side of Brixham Harbour, opposite The Prince William Pub. Your joining times can be found on your confirmation email.

The boats can be recognised as follows:

PILGRIM Black hull and bulwarks with yellow stripe

Brixham transport and parking details

Kit List


  • Sailing Instruction 
  • Safety Equipment (Life jackets and harnesses) 
  • All meals to include refreshments throughout the day
  • Bed linen, duvet, pillows 

What is not included 

  • Waterproof jacket and trousers
  • Alcoholic beverages
  • Towels

What to Bring

Please limit yourself to one soft bag or rucksack as there is limited storage space on board. No suitcases please! 

Pilgrim does not provide waterproofs. So you need to bring waterproof jacket and trousers These don't have to be sailing waterproofs. Any good outdoor waterproofs should keep you warm and dry. If you are sailing on a longer voyage or in early spring or autumn you will find the sailing or mountaineering salopette type waterproof trousers will keep you warmer than walking trousers with waist. If you need any advice please ring us on 01872 580022

  • Waterproof jacket and trousers
  • Hats for sun and cold weather.
  • At least two sets of warm clothes - layers e.g. tracksuit bottoms, shirts, fleece jacket, wool jumpers, thick socks, and neck scarf. It can get cold at sea even in mid summer.
  • Swim suit, towel, and suntan lotion.
  • Flat shoes with a good grip e.g. trainers or sailing deck shoes.
  • Sailing boots or wellies as the sea can come over deck if rough*.
  • (An alternative to boots in summer is to bring another pair of flat shoes with a good grip in case the first pair get wet).
  • All terrain type sandals are great for dinghy trips ashore – but you do need shoes which protect your toes for sailing.
  • Scillies trips – Walking boots are useful and can be these can be worn on Pilgrims deck too
  • A small rucksack is useful for going ashore – especially on sailing and walking and Scillies voyages.
  • Camera, binoculars, sketchbook, a relaxing read.
  • Passport for French Voyages, Reciprocal Free Health Care card in Europe.
  • Please bring a passport on French trips or any 6 day voyage like Scillies where France could be an alternative venue.
  • Any medication, spare spectacles. Seasick tablets - check with your Doctor, which brand if you suffer asthma or are on medication.
  • RYA Cruising Logbook or similar if you want to log your sailing experience e.g. sea miles, night hours
  • Musical instruments are always welcome.

Pilgrim does not always have wine bottles for sale on board so you are welcome to bring modest quantities of alcohol e.g. to drink with evening meals, but drinking whilst sailing is not allowed.



Lovely boat and great crew. No question was too daft. A highly enjoyable education.


This was my first voyage on a tall ship and I had no previous experience of sailing. The crew were wonderful - friendly, calm and patiently explained and gave me confidence to help with sailing the boat. They also helped to build a warm, friendly and fun atmosphere among all of us onboard. I cannot wait until I have the opportunity to sail on Pilgrim again.


Sailing on Pilgrim was amazing. I loved every moment, she is totally beautiful. Swimming ashore and snorkelling. Building a fire on the beach. I love the freedom and peace being on the water, it's so natural and relaxing. I had such a great time with a great bunch of people.


I can't wait for the next time- sailing on Pilgrim isn't just a holiday, it's an adventure full of new experiences, friendship, laughter and fun.


A super day assisted by lovely sun and cloud, sheer joy at being on the water.


Fantastic few days sailing on Pilgrim, the experience was well past my expectations and this was the result of the crew who all worked very hard in making this an unforgettable experience.

Eddie P - Pilgrim Guest Feedback Photo
Eddie P - Pilgrim Guest Feedback Photo

Wow, what can I say about my first trip on the beautiful Pilgrim with Classic Sailing? It was amazing! I am still smiling about the utterly brilliant weekend. I booked this trip as a bit of an escape from the day to day normal life on the land and it was well worth it. I returned home more relaxed, a little sunburnt, but wanting to just jump straight back on board! I t was great fun being allowed to be involved in raising the sails and learning a bit of history about the vessel. If you hare thinking about booking a voyage, be it a day trip, weekend or longer... do it! I could not recommend it more highly and as a single traveller I also felt at ease and safe while on the whole voyage.


Brilliant, fantastic, I could not have wished for better. The crew couldn't do enough for us and made the day even more special. If you want to do something a bit different for a big birthday and something that your guests will talk about for a long time then I would highly recommend Pilgrim.


Pilgrim is a fantastic heritage project that deserves everyones support. I have sailed on her twice now and on both occasions the party has had a most wonderful sailing experience. Get out there and appreciate her!


The trip was one of the best experiences of my life and something I will never forget. Food was wonderful... beds were comfy... crew were faultless and very knowledgeable about the boat and its history. You can tell they have a true passion for their jobs. I would certainly return again and will be recommending to all I know!


Vessel Gallery

Restored Brixham Sailing Trawler Pilgrim in action and images. Photos from Classic Sailing customers, ships crew and professional photographers. We hope it gives a flavour of her sailing, life on board, the people that come, her beautiful sailing grounds and what it is like to live below decks.

Other Voyages


RYA Competent Crew or RYA Day Skipper MK1604023


Sun 16-04-2023

Plymouth, UK


Fri 21-04-2023

Plymouth, UK


Fully Booked


2023 Easter Holiday Sailing Adventure PM070423


Fri 07-04-2023

Brixham, UK


Mon 10-04-2023

Brixham, UK

Limited Spaces Available Sailing holidays on Pilgrim with Classic Sailing




English Riviera and Torbay Airshow PM010623


Thu 01-06-2023

Brixham, UK


Sun 04-06-2023

Brixham, UK

Limited Spaces Available Torbay Airshow, escape the crowds and watch from the water. the best seat in the house



Recently Viewed Voyages


Dartmouth Regatta Cruise PM240823


Thu 24-08-2023

Brixham, UK


Sun 27-08-2023

Brixham, UK

Sailing on Pilgrim with Classic Sailing